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Caribbean beach vacation rentals

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Top-rated vacation rentals in Caribbean

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

  1. Entire villa
  2. Las Terrenas
Amazing sea view luxury modern, fully staffed

Casa Phil is an architecturally designed villa that was built with the objective of creating a large and beautifully appointed home that is both family-friendly and secured for small children. Included are concierge, daily cleaning and cooking service staff to make your stay truly unforgettable and make sure you don't have to worry about anything during your vacation. Home office ready with a fiber internet connection and all-house Wi-Fi.

$518 per night
  1. Entire home
  2. Grand Cayman
Lone Palm by Grand Cayman Villas

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$840 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Les Terres Basses
Bamboo
$714 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Caribbean vacation rentals

SUPERHOST
  1. Entire guest suite
  2. San Juan
Treehouse w floating deck at La Botanica
$190 per night
  1. Entire home
  2. Grand Cayman
Pools of the Kai #3 by Grand Cayman Villas
$476 per night
SUPERHOST
  1. Dome
  2. Ponce
Bubble Puerto Rico
$333 per night
SUPERHOST
  1. Private room
  2. La Habana
Casa Blanca B&B with beautiful terrace &sea views
$33 per night
SUPERHOST
  1. Entire condo
  2. Rum Point
Starfish Paradise Beachfront Condo
$288 per night
SUPERHOST
  1. Entire cottage
  2. Runaway Bay
Bahia - Charming beach cottage, loft/wood shutters
$270 per night
SUPERHOST
  1. Private room
  2. Vinales
EL BOHÍO DE DIEGO + WIFI + HOTEL POOL
$20 per night
SUPERHOST
  1. Entire condo
  2. Nassau
Paradise Hideaway Modern New 1 Bedroom 1 Bath Pool
$179 per night
SUPERHOST
  1. Entire rental unit
  2. Atalaya
Garden Apartment II at Ocaso Luxury Villa
$174 per night
SUPERHOST
  1. Entire home
  2. Pompano Beach
RENT LUXE 5 STAR 5 BED HTD POOL+HOT TUB STUNNING!
$449 per night
SUPERHOST
  1. Entire condo
  2. Rum Point
Nature's View: Pools of the Kai #2
$309 per night
SUPERHOST
  1. Entire vacation home
  2. Sainte-Anne
Sun Dreams - Lodge Sweet Sunset with Sea View
$124 per night

Caribbean house rentals

  1. Entire home
  2. North Side
Ocean's Edge: Beachfront Home with Rooftop Views
$416 per night
  1. Entire home
  2. Stake Bay
Modern Oceanfront, 2Primary Suites, sleeps 6, pool
$375 per night
SUPERHOST
  1. Entire home
  2. Key West
Grand Home/Heated, Salt Water Pool/Dog Friendly
$307 per night
SUPERHOST
  1. Entire home
  2. Fort Lauderdale
★Near Downtown & Beach- Luxury House /Heated spa★
$358 per night
  1. Entire home
  2. Grand Cayman
Kai Tana by Grand Cayman Villas
$504 per night
  1. Entire home
  2. Placida
Camp GoodNow: Stunning new beachfront home, private balcony off master!
$440 per night
SUPERHOST
  1. Entire home
  2. Miami
ULTRA LUXURIOUS VILLA 4/3 LARGE POOL PFCT GETAWAY
$315 per night
SUPERHOST
  1. Entire home
  2. San Cayetano de Venecia
Quinta La Ceiba Modern Home with Pool in DairyFarm
$193 per night
SUPERHOST
  1. Entire home
  2. Cape Coral
Completely Remodeled 3 Bedroom Home With A Pool
$175 per night
  1. Entire home
  2. Cape Coral
NEW! Waterfront Cape Coral Oasis w/ Private Pool!
$333 per night
SUPERHOST
  1. Entire home
  2. Tower Isle
Tranquil Times Villa Jamaica
$470 per night
SUPERHOST
  1. Entire home
  2. Guayama
Completely private, for couples.
$107 per night

Beach house rentals in Caribbean

SUPERHOST
  1. Entire home
  2. Fort Myers Beach
Onda Dolce Blue. Beachfront house with ocean views
$165 per night
SUPERHOST
  1. Entire home
  2. Siesta Key
Beachfront Getaway in Siesta Key
$252 per night
  1. Entire home
  2. St. Thomas
Stunning Water Views
$590 per night
SUPERHOST
  1. Entire home
  2. Marco Island
Luxury 4 Bedroom House ⭐️ Heated Pool ⭐️ Near Beach
$395 per night
  1. Entire home
  2. Luquillo
La orilla beach house
$859 per night
SUPERHOST
  1. Entire home
  2. Medianía Alta
Large Ocean Front Home on Sandy Beach With Pool
$478 per night
SUPERHOST
  1. Entire home
  2. Saint James City
ISLAND VIBE 3/2 with SALT WATER HEATED POOL on water with HOT TUB!
$200 per night
  1. Entire home
  2. Captiva
Captiva Charm - Gulf front Olde Captiva style cottage
$589 per night
  1. Entire home
  2. Naples
VILLA CASCATA - Tropical Oasis, Ideal Location!
$515 per night
SUPERHOST
  1. Entire home
  2. George Town
Eden Hill / Extraordinary Views / Great Location
$345 per night
SUPERHOST
  1. Entire home
  2. Frederiksted
Rainbow Beach Dreams
$250 per night
  1. Entire home
  2. Cap-Haitien
Rockaway
$170 per night

Your guide to Caribbean

All About the Caribbean

The Caribbean is made up of 26 island countries surrounded by bejeweled blue and green waters and is known around the world as a holiday paradise. People flock here, especially in the winter, for warm sands, golden sunshine, and that sense of island time abandon — plus, the fruity drinks under towering palm trees. The Dominican Republic is the most visited of all the islands due to its vibrant city and cultural life and postcard-perfect beaches. West of that is Cuba, famous for its Old World architecture, rich jazz and music scenes, and several UNESCO World Heritage Sites. Closer to South America is little St. Lucia, known for its rainforests, colorful coral reefs (perfect for diving and snorkeling), and, of course, pristine beaches surrounded by the island’s volcanic peaks.

The countries in the Caribbean are extremely diverse, not only in their histories, cultures, and languages, but their landscapes and topographies. For example, vibrant Jamaica could not be more different from super-chill Aruba and swanky St. Barts. So whether you’re seeking an island that’s large or small, glitzy or low-key, in the Caribbean there is a sanctuary for everyone.


When is the best time to stay in a vacation rental in Caribbean?

Thanks to trade winds, the weather in the Caribbean is sunny and pleasant all year round. The only caveat is that tropical storms and hurricanes occur to varying degrees of intensity here, and their likelihood increases from about July to November. But it’s the dry season from December through March that makes the region so popular. Villas to rent in the Caribbean are in demand during the winter, as many feel the urge to escape the colder weather up north and take in the sun, fun, and the many festivals — like Trinidad’s Carnival, the biggest of the Caribbean’s carnivals, and the Bahamas’ Junkanoo, a cultural street festival and celebration dating back centuries that takes place between Boxing and New Year’s Day. There are also plenty of Caribbean rentals in May and June, if you don’t mind the chance of a little rain.


What are the top things to do in Caribbean?

Santo Domingo

Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited colonial settlement in the Western Hemisphere and was founded in 1496. The historic city center, Zona Colonial, is a UNESCO World Heritage Site, with cobblestone streets, colorful houses, and colonial-style architecture and structures like the 16th-century Basilica Cathedral of Santa María la Menor, the oldest surviving cathedral in the Americas.

Curaçao

Sitting off the coast of Venezuela is the Dutch island of Curaçao, lesser known than its neighbors, but with just as much to offer — including its lack of hurricane seasons. Willemstad, the capital, is one of the few UNESCO World Heritage cities in the Caribbean, and it’s pulsing with nightlife and festivals like Carnival and King’s Day. The diving here is top-notch, there are dozens of stunning beaches to choose from, and the lodging ranges from hostels to five-star resorts — so there’s something here for everyone.

Reggae in Jamaica

Jamaica is the birthplace of reggae. The music took off in the late 1960s, and by the 1970s, with the superstardom of Bob Marley and the Wailers, it became known throughout the world. If you’re in Kingston, check out the clubs, still playing the dub style that made the genre so popular. The best of the best musicians have been known to play at the annual reggae festival held in June.